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Anticlimax Boss: The Kimono Girls in the Heart Gold Nuzlocke. Thanks to the Choice Scarf, Dick Pinch the Pinsir sweeps all of them except Flareon, and only Vaporeon even gets off a hit. To the same degree, Sabrina, who Dick Pinch sweeps in three turns.
Tear Jerker: Some of his deaths in his Nuzlocke series, including Qwerty the Prinplup in Diamond, Bugsy the Venonat in Emerald Randomizer, STD the Kingler in Heartgold, and Snowball the Golem in the latter. Fire Red Omega was full of them, namely Billy the Manectric, Mollee the Houndoom and Pearl the Kingdra.
What an Idiot: He's had quite a few in his Nuzlockes, but most notably the Fire Red Omega finale, where Dicks' Meganium was asleep and easily open to a 2HKO by Frostitute the Jynx, and instead of doing that, he switches into Tits the Castform, who, after a long-winded bout, dies to an Overgrow boosted Frenzy Plant.